Synthetic resin and process of making the same



ll altented ass. 12, 1932 STATES PATENT OFFICE WHJLMM HENRY MOSS AN DBLANCHE BABETTE WHITE, OF CUMBERLAND, MARYLAND,

ASSIGNORS TO CELANESE CORPORATION OF AMERICA, A CORPORATION OF DELA-wean SYNTHETIC RESIN AND PROCESS OF MAKING THE SAME No Drawing.

' This invention relates to the preparation of a synthetic resin fromtoluene sulfonamid, and also to coating or plastic compositionscontaining derivatives of cellulose, and 5 particularly organicderivatives of cellulose. An object of our invention is to prepare asynthetic. resin that is compatible with derivatives of cellulose, andtherefore suitable for use in the films, lacquers or other [0 coatingcompositions or plastics containing such derivatives of cellulose.

A further obect of our invention is to provide a suitable resin forlacquers or plastic compositions containing organic substitutionproducts of cellulose such as cellulose acetate, which resin iscompatible with the other constituents of the lacquers and whichproduces clear solutions which, upon drying, form films that areadherent, tough, hard and water'repellant. V i v The preparation of alacquer containing Organic derivatives of cellulose such as celluloseacetate as the main constituent of the lacquer base, which lacquer is tobe applied to a hard, smooth surface, presents many difficulties. Thisis due primarily to the fact that films from lacquers containingcellulose acetate as the sole constituent of the lacquer base do notadhere to smooth surfaces. When attempts are made to incorporatenaturakgums or resins in the lacquer containing cellulose acetate inorderto impart the necessary adhesive qualities to the films producedfrom it, both the lacquer and the films We have foundthat the syntheticresins produced from aromatic sulfonamid, such as toluene sulfonamid andbenzaldehyde are compatible with cellulose acetate, and that when addedto lacquers containing cellulose acetate they form clear solutions that,upon drying, produce clear, hard, tough and firmly adherent films. l i

lhe selection of a suitable resin for a lacquer containing the organicderivatives of cellulose'presents a 'difiicult problem because theresin'must be compatible with the organic derivatives; such as celluloseacetate, both in solution andin the dry films and produced become cloudyand unhomogeneous.

also with softeners, pigmen dyes which Application filed Noveniber 17,1928. Serial K001320311.

may be added to produce desired efiects and variations of the films. Ingeneral, a synthetic resin for this pur ose should be easily preparedfrom preihrably cheap materials, it shouldbe free of or easily freedvfrom any catalysts, either acid or-alkaline, used in its preparation,itshould of itself be practically neutral and should be stronglyresistant to water and free fromwater soluble materials.

We have found that the special resins prepared from toluene sulfonamidand benzaldehyde in the absence of a catalyst or in the presence ofeither acid or alkaline catalysts can be used as above stated in,cellulose derivative lacquers or plastic compositions.

In accordance with our invention, we prepare a synthetic resin formed bythe cons densatioh of an aromatic sulfonamid such as toluene sulfonamid,benzene sulfonamid,

or xylene sulfonamid, and benzaldehyde.

This synthetic resin is then used for making a lacquer or a plasticcomposition which contains one or more derivatives of cellulose and avolatile solvent. The lacquer may also contain one or more natural orsemi-synthetic resins or gums, one or more plastifiers or softeningagents, medium and/or high boiling ing the solutions containing thespecial resin and a derivative of cellulose through the orifices of aspinnerette, either into *a heated into a precipitating-bath, as in wetspinnlng.

The solution may also be employed as an a hesive, and is particularlyuseful in this coning celluloid sheets toadhere to surfaces of sheets ofglass betweenwhich they are placed.

The plastic containing derivatives of-cellulose and our resin, may beworked into sheets which may'also be usedfor laminated glass,

and alsomay be worked into blocks 'or articles in any known manner.

evaporative atmosphere as in dry spinning, or

nection for making shatterless glass by caus I The derivatives ofcellulose that may be used for making solutions, coating or plasestersof cellulose, such as cellulose acetate,

cellulose formate, cellulose propionate, or cellulose butyrate andcellulose ethers, such as ethyl cellulose, methyl cellulose, or benzy'lcellulose. a

The low boiling point solvent that may be employed may be one or amixture of two or more of the following: acetone, alcohol, benzene orethylene dichloride. Examples of medium and/or high boiling solventsare: ethyl acetate, ethyl lactate, tetrachlorethane, benzyl alcohol ordiacetone alcohol. Examples of suitable plasticizers are: diphenylolpropane, monomethyl xylene, sulfonamid, ortho or meta ethyl toluenesulfonamid. If desired, fire retardants may be added, particularly thevery effective bromine derivativesof organic compounds, such as bromi-'nated tricresyl phosphate.

The pigments or dyes that may be used are any of the ordinary pigmentsor dyes used in the paint or lacquer industry.

Of the natural gums or resins that may be employed, the following may bementioned: manila, accroides, pontianak,kauri, dammar, rosin andshellac.

The semi-synthetic resin estergum, which is the glycerol ester of rosin,may also be added. Examples of other synthetic resins that may be usedin conjunction with our resin, are the fusible and solublephenolformaldehyde, diphenylol propane-formaldehyde preferably preparedin the presence of acid catalysts, and phenol-furfural resins andtoluene sulfonamid and formaldehyde resins.

The following is a detailed description of one mode of preparing ourresin:

Equimolecular proportions of paratoluene I sulfonamid and benzaldehydeare heated together under re'fluxfor'S hours at 150 C.

' A- resin is obtained, which is washed with water to' remove excess!reactants, and is then freed from water by distillation or by dry- 5inug in-the air. Catalysts, neutral, acid or. a a

is soluble'irr acetone and alcohol, andlargely line'may be added asdesired. The resin insoluble in benzene. The toluene sulfonamid that isemploy ;may be a'pure product having a meltmgpoint of 137, or it may bea commercial'product having a lower melting point. 7 The benzaldehydemay be a pureproduct or a commercial one. --While equi molecularproportions are preferred, the pro portions used may be variedconsiderably.

The resin formed by the above method has a. meltin point of from to C.It is complete y compatible in call proportions with cellulose acetatein films, 'plastics,-

threads, lacquers, etc. It is to be understood that whilst othersynthetic resins, as mentioned above, may be used with our resin, it isalso permissible to prepare a complex resin at the same time. That is,for example, a mixture of formaldehyde and benzaldehyde, or of furfuraland benzaldehyde may be condensed with the toluene sulfonamid, and otherproducts such as urea, phenol, analine, acetone, etc., may be added tothe reaction mixture together with a larger quantity of aldehyde so thata complex resin is produced. The resin thus produced is suitable formixture with cellulose acetate and cellulose derivatives to producefilms, plastics, threads, lacquers, etc.

Owing to the complete compatibility with cellulose acetate the resin isparticularly suitable for admixture with it in any of the numeroustechnical applications of this ester. It may be used in smallproportions to make films which have greater tensile strength than filmsfromthecellulose ester alone. Such films are suitable for protectivecoatings on cloth, fabric, wire, leather, etc., and may be manufactureof artificial silk. In larger proportions, it is especially useful incellulose acetate lacquers, plastics, and in solutions for use asadhesive.

It is to be understood that the foregoing detailed description is givenmerely .by way of illustration, and that many variations may be madetherein without departing from the spirit of our invention.

Havingthus-described our invention, what we desire to claim and secureby Letters Pat'- ent is:

1. Methodof preparing a synthetic resin comprising reacting an aromaticsulfonamid with benzaldeh de.

2. Method 0 preparing a. synthetic resin comprising reactmg toluenesulfonamid with benzaldehyde. J

3. Method of preparing a synthetic resin comprising heating an aromaticsulfonamid with benzaldeh do for about 8 hours.

4. Method Of PIGPaIiIig IL synthetic resin comprising heating toluenesulfonamid with ,benz'aldehyde for about 8 hours.

5. A synthetic resin repared by reacting an aromatic sulfonami withb'enzaldehyde.

by reacting toluene sulfonamid,-sai resin having a melting point ofbetween about'50 to 60 C.

.In testimony whereof, we have hereunto subscribed our names.

. WILLIAM HENRY MOSS.

BLANGHE B,

